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3. Agent John Connolly

Outfit: Federal Bureau of Investigation

Crime: John Connolly was the FBI handler for Boston gangsters Whitey Bulger and Steve Flemmi. Connolly was convicted in federal court on charges of racketeering and obstruction of justice in 2002—he'd let his childhood buddies Bulger and Flemmi know the feds were seeking to prosecute the men for a book-length list of crimes like drug trafficking and homicide.

Connolly was convicted in a state court of 2nd degree murder—his tip to Bulger and Flemmi about witnesses in investigations into the mobsters' activities led to hits that occurred in 1981 and '82.